RU2122432C1 - Контрастные агенты и их применение - Google Patents
Контрастные агенты и их применение Download PDFInfo
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- RU2122432C1 RU2122432C1 RU94045927A RU94045927A RU2122432C1 RU 2122432 C1 RU2122432 C1 RU 2122432C1 RU 94045927 A RU94045927 A RU 94045927A RU 94045927 A RU94045927 A RU 94045927A RU 2122432 C1 RU2122432 C1 RU 2122432C1
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- 239000002872 contrast media Substances 0.000 title claims abstract description 29
- 229920000642 polymer Polymers 0.000 claims abstract description 234
- 239000007789 gas Substances 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 125000000962 organic group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920002988 biodegradable polymer Polymers 0.000 claims abstract description 7
- 239000004621 biodegradable polymer Substances 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 230000015572 biosynthetic process Effects 0.000 claims description 39
- 239000011859 microparticle Substances 0.000 claims description 38
- -1 hydroxy, carbonyl Chemical group 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229920001184 polypeptide Polymers 0.000 claims description 9
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 9
- 238000002604 ultrasonography Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 8
- 150000004676 glycans Chemical class 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229920001282 polysaccharide Polymers 0.000 claims description 7
- 239000005017 polysaccharide Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 229920003169 water-soluble polymer Polymers 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims 1
- 229920006037 cross link polymer Polymers 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 63
- 239000000126 substance Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 148
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
- 239000000047 product Substances 0.000 description 83
- 238000002474 experimental method Methods 0.000 description 75
- 239000002904 solvent Substances 0.000 description 72
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- 239000000203 mixture Substances 0.000 description 64
- 238000005160 1H NMR spectroscopy Methods 0.000 description 61
- 239000011541 reaction mixture Substances 0.000 description 61
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 238000003756 stirring Methods 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000839 emulsion Substances 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- 230000003287 optical effect Effects 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 26
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- 238000001542 size-exclusion chromatography Methods 0.000 description 26
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 25
- 239000007864 aqueous solution Substances 0.000 description 24
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 22
- 239000000725 suspension Substances 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
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- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 20
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 18
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- 239000000460 chlorine Substances 0.000 description 17
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- FDIHYONBFVCOPU-UHFFFAOYSA-N 2-methylprop-2-enoyloxymethyl benzoate Chemical compound CC(=C)C(=O)OCOC(=O)C1=CC=CC=C1 FDIHYONBFVCOPU-UHFFFAOYSA-N 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- 238000004108 freeze drying Methods 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- GALGFDDHBGDRFQ-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)OC(C)OC(=O)C(C)=C GALGFDDHBGDRFQ-UHFFFAOYSA-N 0.000 description 10
- HKYFLUZPQFOABT-UHFFFAOYSA-N 16-hydroxyhexadecanoyloxymethyl 16-hydroxyhexadecanoate Chemical compound OCCCCCCCCCCCCCCCC(=O)OCOC(=O)CCCCCCCCCCCCCCCO HKYFLUZPQFOABT-UHFFFAOYSA-N 0.000 description 10
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 108090000371 Esterases Proteins 0.000 description 10
- JYWJULGYGOLCGW-UHFFFAOYSA-N chloromethyl chloroformate Chemical compound ClCOC(Cl)=O JYWJULGYGOLCGW-UHFFFAOYSA-N 0.000 description 10
- MKEVFCHVGWJVEU-UHFFFAOYSA-N ethoxycarbonyloxymethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)OCOC(=O)C(C)=C MKEVFCHVGWJVEU-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 238000010526 radical polymerization reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 9
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 9
- 235000011130 ammonium sulphate Nutrition 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
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- 238000000576 coating method Methods 0.000 description 8
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- 230000007062 hydrolysis Effects 0.000 description 8
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- WAIFIHKBNYUZGZ-UHFFFAOYSA-N 1-(2-methylprop-2-enoylamino)propan-2-yloxycarbonyloxymethyl acetate Chemical compound CC(=C)C(=O)NCC(C)OC(=O)OCOC(C)=O WAIFIHKBNYUZGZ-UHFFFAOYSA-N 0.000 description 7
- 229920001400 block copolymer Polymers 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- CVASMYWHWRNWOX-UHFFFAOYSA-N chloro methyl carbonate Chemical compound COC(=O)OCl CVASMYWHWRNWOX-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
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- 125000000524 functional group Chemical group 0.000 description 7
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- 108090000623 proteins and genes Proteins 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ZHESMCIWZWYNLC-UHFFFAOYSA-N 2-methylprop-2-enoyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(=O)C(C)=C ZHESMCIWZWYNLC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
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- 230000006378 damage Effects 0.000 description 6
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- 238000001914 filtration Methods 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- JUALYYGOQNLSOT-UHFFFAOYSA-N methoxycarbonyloxymethyl 2-methylprop-2-enoate Chemical compound COC(=O)OCOC(=O)C(C)=C JUALYYGOQNLSOT-UHFFFAOYSA-N 0.000 description 6
- OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 0.000 description 6
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- 230000007017 scission Effects 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- HRBNXCSWUDHDLM-UHFFFAOYSA-N 1-methoxycarbonyloxyethyl 2-methylprop-2-enoate Chemical compound COC(=O)OC(C)OC(=O)C(C)=C HRBNXCSWUDHDLM-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
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- 229960000583 acetic acid Drugs 0.000 description 5
- 238000006065 biodegradation reaction Methods 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical group NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- TVDCUCKBZCDWRS-UHFFFAOYSA-N phenylmethoxycarbonyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(=O)OCC1=CC=CC=C1 TVDCUCKBZCDWRS-UHFFFAOYSA-N 0.000 description 5
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- LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- 108091006905 Human Serum Albumin Proteins 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
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- UIRNOIFHMQKWFT-UHFFFAOYSA-N [ethenoxycarbonyloxy(phenyl)methyl] acetate Chemical compound C=COC(=O)OC(OC(=O)C)C1=CC=CC=C1 UIRNOIFHMQKWFT-UHFFFAOYSA-N 0.000 description 4
- PDQDJZLOMGSJFK-UHFFFAOYSA-N acetyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(C)=O PDQDJZLOMGSJFK-UHFFFAOYSA-N 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
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- RGPYVAUWRFGVHX-UHFFFAOYSA-N 1-[1-(2-methylprop-2-enoylamino)propan-2-yloxycarbonyloxy]ethyl acetate Chemical compound CC(=C)C(=O)NCC(C)OC(=O)OC(C)OC(C)=O RGPYVAUWRFGVHX-UHFFFAOYSA-N 0.000 description 3
- CERXDWLUWLFFEK-UHFFFAOYSA-N 1-chloroethyl methyl carbonate Chemical compound COC(=O)OC(C)Cl CERXDWLUWLFFEK-UHFFFAOYSA-N 0.000 description 3
- VOWDCCFXULVMDY-UHFFFAOYSA-N 16-trityloxyhexadecanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCCCCCCCCCCCCCCC(=O)O)C1=CC=CC=C1 VOWDCCFXULVMDY-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- SEEYHRCMNMPHDG-UHFFFAOYSA-N 2-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OCCCl SEEYHRCMNMPHDG-UHFFFAOYSA-N 0.000 description 3
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920002307 Dextran Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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Images
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
- A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/223—Microbubbles, hollow microspheres, free gas bubbles, gas microspheres
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GB929204920A GB9204920D0 (en) | 1992-03-06 | 1992-03-06 | Improvements in or relating to contrast agents |
GB9204920.4 | 1992-03-06 | ||
GB9204918.8 | 1992-03-06 |
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RU94045927A RU94045927A (ru) | 1996-11-10 |
RU2122432C1 true RU2122432C1 (ru) | 1998-11-27 |
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RU94045927A RU2122432C1 (ru) | 1992-03-06 | 1993-03-05 | Контрастные агенты и их применение |
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JP (1) | JP3650393B2 (fr) |
CN (1) | CN1084410A (fr) |
AT (1) | ATE184491T1 (fr) |
AU (1) | AU676467B2 (fr) |
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DE (1) | DE69326447T2 (fr) |
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ES (1) | ES2135466T3 (fr) |
FI (1) | FI944077A0 (fr) |
HU (1) | HUT68612A (fr) |
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GB9106686D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
US5205290A (en) * | 1991-04-05 | 1993-04-27 | Unger Evan C | Low density microspheres and their use as contrast agents for computed tomography |
MX9205298A (es) * | 1991-09-17 | 1993-05-01 | Steven Carl Quay | Medios gaseosos de contraste de ultrasonido y metodo para seleccionar gases para usarse como medios de contraste de ultrasonido |
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US6383470B1 (en) | 1992-09-26 | 2002-05-07 | Thomas Fritzsch | Microparticle preparations made of biodegradable copolymers |
IL108416A (en) | 1993-01-25 | 1998-10-30 | Sonus Pharma Inc | Colloids with phase difference as contrast ultrasound agents |
US5558855A (en) * | 1993-01-25 | 1996-09-24 | Sonus Pharmaceuticals | Phase shift colloids as ultrasound contrast agents |
CZ191695A3 (en) * | 1993-01-25 | 1996-05-15 | Sonus Pharma Inc | Biologically compatible contrast agent, process of its preparation and representation method by ultrasound |
GB9305351D0 (en) * | 1993-03-16 | 1993-05-05 | Nycomed Imaging As | Improvements in or relating to contrast agents |
GB9318288D0 (en) * | 1993-09-03 | 1993-10-20 | Nycomed Imaging As | Improvements in or relating to contrast agents |
HU225495B1 (en) | 1993-12-15 | 2007-01-29 | Bracco Research Sa | Gas mixtures useful as ultrasound contrast media |
GB9402867D0 (en) * | 1994-02-15 | 1994-04-06 | Nycomed Imaging As | Improvements in or relating to contrast agents |
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GB9622711D0 (en) * | 1996-10-31 | 1997-01-08 | British Tech Group | Instrument having enhanced ultrasound visibility |
US20020159951A1 (en) * | 1997-05-06 | 2002-10-31 | Unger Evan C. | Novel targeted compositions for diagnostic and therapeutic use |
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US20010003580A1 (en) | 1998-01-14 | 2001-06-14 | Poh K. Hui | Preparation of a lipid blend and a phospholipid suspension containing the lipid blend |
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US6725083B1 (en) | 1999-02-02 | 2004-04-20 | Senorx, Inc. | Tissue site markers for in VIVO imaging |
US8498693B2 (en) | 1999-02-02 | 2013-07-30 | Senorx, Inc. | Intracorporeal marker and marker delivery device |
US6862470B2 (en) | 1999-02-02 | 2005-03-01 | Senorx, Inc. | Cavity-filling biopsy site markers |
US7983734B2 (en) | 2003-05-23 | 2011-07-19 | Senorx, Inc. | Fibrous marker and intracorporeal delivery thereof |
US20090030309A1 (en) | 2007-07-26 | 2009-01-29 | Senorx, Inc. | Deployment of polysaccharide markers |
US7651505B2 (en) | 2002-06-17 | 2010-01-26 | Senorx, Inc. | Plugged tip delivery for marker placement |
US8361082B2 (en) | 1999-02-02 | 2013-01-29 | Senorx, Inc. | Marker delivery device with releasable plug |
US9820824B2 (en) | 1999-02-02 | 2017-11-21 | Senorx, Inc. | Deployment of polysaccharide markers for treating a site within a patent |
US6575991B1 (en) | 1999-06-17 | 2003-06-10 | Inrad, Inc. | Apparatus for the percutaneous marking of a lesion |
US7311893B2 (en) * | 2000-07-25 | 2007-12-25 | Neurochem (International) Limited | Amyloid targeting imaging agents and uses thereof |
EP2319449B1 (fr) | 2000-11-20 | 2016-03-09 | Senorx, Inc. | Marqueurs de sites tissulaires pour l' imagerie in vivo |
GB0128052D0 (en) | 2001-11-22 | 2002-01-16 | Drug Discovery Lab As | Compounds |
AUPR951501A0 (en) * | 2001-12-14 | 2002-01-24 | Smart Drug Systems Inc | Modified sustained release pharmaceutical system |
US7462366B2 (en) | 2002-03-29 | 2008-12-09 | Boston Scientific Scimed, Inc. | Drug delivery particle |
DE10224352A1 (de) * | 2002-06-01 | 2003-12-11 | Mueller Schulte Detlef | Thermosensitive Polymerträger mit veränderbarer physikalischer Struktur für die biochemische Analytik, Diagnostik und Therapie |
WO2003105917A2 (fr) | 2002-06-12 | 2003-12-24 | Scimed Life Systems, Inc. | Agents gonflants |
US7842377B2 (en) | 2003-08-08 | 2010-11-30 | Boston Scientific Scimed, Inc. | Porous polymeric particle comprising polyvinyl alcohol and having interior to surface porosity-gradient |
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US7883490B2 (en) | 2002-10-23 | 2011-02-08 | Boston Scientific Scimed, Inc. | Mixing and delivery of therapeutic compositions |
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US7877133B2 (en) | 2003-05-23 | 2011-01-25 | Senorx, Inc. | Marker or filler forming fluid |
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- 1993-03-05 CZ CZ942148A patent/CZ284844B6/cs not_active IP Right Cessation
- 1993-03-05 EP EP93905527A patent/EP0627942B1/fr not_active Expired - Lifetime
- 1993-03-05 IL IL104963A patent/IL104963A/xx not_active IP Right Cessation
- 1993-03-05 SG SG1996005321A patent/SG44668A1/en unknown
- 1993-03-05 CA CA002130670A patent/CA2130670A1/fr not_active Abandoned
- 1993-03-05 BR BR9306044A patent/BR9306044A/pt not_active Application Discontinuation
- 1993-03-05 SK SK1066-94A patent/SK106694A3/sk unknown
- 1993-03-05 WO PCT/GB1993/000470 patent/WO1993017718A1/fr active IP Right Grant
- 1993-03-05 RU RU94045927A patent/RU2122432C1/ru active
- 1993-03-05 AU AU36424/93A patent/AU676467B2/en not_active Ceased
- 1993-03-05 PL PL93305025A patent/PL174114B1/pl unknown
- 1993-03-05 CN CN93104052A patent/CN1084410A/zh active Pending
- 1993-03-05 DE DE69326447T patent/DE69326447T2/de not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
CN1084410A (zh) | 1994-03-30 |
EP0627942B1 (fr) | 1999-09-15 |
WO1993017718A1 (fr) | 1993-09-16 |
EP0627942A1 (fr) | 1994-12-14 |
IL104963A0 (en) | 1993-07-08 |
JPH07505148A (ja) | 1995-06-08 |
CZ284844B6 (cs) | 1999-03-17 |
HUT68612A (en) | 1995-07-28 |
DE69326447D1 (de) | 1999-10-21 |
SG44668A1 (en) | 1997-12-19 |
BR9306044A (pt) | 1997-11-18 |
AU676467B2 (en) | 1997-03-13 |
OA10096A (en) | 1996-12-18 |
LV10396B (en) | 1996-02-20 |
EE03079B1 (et) | 1998-04-15 |
CZ214894A3 (en) | 1995-04-12 |
IL104963A (en) | 1997-09-30 |
HU9402565D0 (en) | 1994-11-28 |
NO943272L (no) | 1994-09-05 |
JP3650393B2 (ja) | 2005-05-18 |
NZ249548A (en) | 1996-08-27 |
NO943272D0 (no) | 1994-09-05 |
SK106694A3 (en) | 1995-08-09 |
PL174114B1 (pl) | 1998-06-30 |
US5795562A (en) | 1998-08-18 |
ES2135466T3 (es) | 1999-11-01 |
BG99072A (bg) | 1995-09-29 |
FI944077A (fi) | 1994-09-05 |
RU94045927A (ru) | 1996-11-10 |
DE69326447T2 (de) | 2000-05-18 |
LV10396A (lv) | 1995-02-20 |
CA2130670A1 (fr) | 1993-09-07 |
ATE184491T1 (de) | 1999-10-15 |
AU3642493A (en) | 1993-10-05 |
FI944077A0 (fi) | 1994-09-05 |
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